Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship

Fedor M Miloserdov; Mariia S Kirillova; Michael E Muratore; Antonio M Echavarren

doi:10.1021/jacs.7b13484

Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship

J Am Chem Soc. 2018 Apr 25;140(16):5393-5400. doi: 10.1021/jacs.7b13484. Epub 2018 Feb 22.

Authors

Fedor M Miloserdov¹, Mariia S Kirillova¹, Michael E Muratore¹, Antonio M Echavarren^{1

2}

Affiliations

¹ Institute of Chemical Research of Catalonia (ICIQ) , Barcelona Institute of Science and Technology , Av. Països Catalans 16 , 43007 Tarragona , Spain.
² Departament de Química Orgànica i Analítica , Universitat Rovira i Virgili , C/Marcel·lí Domingo s/n , 43007 Tarragona , Spain.

Abstract

The total synthesis of seven members of the lapidilectine and grandilodine family of alkaloids has been accomplished in racemic and enantiopure form without protection/deprotection of functional groups. The two key steps, an 8- endo-dig hydroarylation and a 6- exo-trig photoredox cyclization, were catalyzed using gold. A rationale for the formation of the cyclopropane ring of the lundurines is also provided.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemical synthesis*
Alkaloids / chemistry
Azocines / chemical synthesis*
Azocines / chemistry
Catalysis
Cyclization
Gold / chemistry
Indole Alkaloids / chemical synthesis*
Indole Alkaloids / chemistry
Indoles / chemical synthesis*
Indoles / chemistry
Models, Molecular
Oxidation-Reduction
Stereoisomerism

Substances

Alkaloids
Azocines
Indole Alkaloids
Indoles
grandilodine A
lapidilectine B
Gold